Substituted diphenyl ether herbicides and process for use

Abstract

This invention relates to substituted diphenyl ethers having selective herbicidal properties and having the formula: ##STR1## wherein R is a saturated or unsaturated, straight chain or branched aliphatic hydrocarbon radical of from 1 to 18 carbon atoms wherein one or more of the --CH 2 -- groups can be replaced with --O--, --S--, --S--S--, --SO--, --SO 2 -- or --NR 2 -- and said hydrocarbon radical is optionally substituted with halogen, trihalomethyl, cyano, aryl, hydroxy, alkoxy, nitro or cycloalkyl having 3 to 6 carbon atoms; R 1 is ##STR2## R 3 is ##STR3## R 2 is hydrogen or a saturated or unsaturated straight or branched chain aliphatic radical having from 1 to 8 carbon atoms, optionally substituted with halogen, hydroxy, alkoxy, cyano or nitro; R 4 and R 5 are independently a saturated or unsaturated, straight or branched chain aliphatic radical having 1 to 8 carbon atoms optionally substituted with halogen, trihalomethyl, alkoxy or cyano; hydrogen or phenyl optionally substituted with halogen, alkyl, alkoxy, trihalomethyl, nitro or cyano; R 6 is a saturated or unsaturated straight chain or branched aliphatic radical containing from 1 to 8 carbon atoms, optionally substituted with halogen, trihalomethyl, cyano, hydroxy, nitro, acetoxy, alkoxy, thioalkoxy or aryl; an aryl radical optionally substituted with halogen, trihalomethyl, hydroxy, cyano, nitro, alkyl or alkoxy; a cyclic 3-6 membered ring alkylene or 5-6 membered ring alkenylene or benzyl optionally substituted with halogen, trihalomethyl, alkyl, hydroxy, alkoxy or cyano; R 7 is an alkylene diradical having from 1 to 6 carbon atoms; X and X' are each independently --O--, --S-- or --NR 2 -- L, M and N are each independently hydrogen, hydroxy, halogen, trihalomethyl, nitro, cyano, alkyl or alkoxy having from 1 to 4 carbon atoms and ##STR4## m has a value of from 1 to 6 and n in each instance has a value of from 0 to 1.

What is claimed is: 
     
       1. A herbicidal compound having the formula ##STR61## wherein R is a saturated or unsaturated, straight chain or branched aliphatic hydrocarbon radical of from 1 to 18 carbon atoms wherein one or more of the --CH 2  -- groups can be replaced with --O--, --S--, --S--S--, --SO--, --SO 2  -- or --NR 2  -- and said hydrocarbon radical is optionally substituted with halogen, trihalomethyl, cyano, aryl, hydroxy, alkoxy, nitro or cycloalkyl having 3 to 6 carbon atoms; R 1  is ##STR62## R 3  is ##STR63## R 2  is hydrogen or a saturated or unsaturated straight or branched chain aliphatic radical having from 1 to 8 carbon atoms, optionally substituted with halogen, hydroxy, alkoxy, cyano or nitro;   R 4  and R 5  are independently a saturated or unsaturated, straight or branched chain aliphatic radical having 1 to 8 carbon atoms optionally substituted with halogen, trihalomethyl, alkoxy or cyano; hydrogen or phenyl optionally substituted with halogen, alkyl, alkoxy, trihalomethyl, nitro or cyano;   R 6  is a saturated or unsaturated straight chain or branched aliphatic radical containing from 1 to 8 carbon atoms, optionally substituted with halogen, trihalomethyl, cyano, hydroxy, nitro, acetoxy, alkoxy, thioalkoxy or aryl; an aryl radical optionally substituted with halogen, trihalomethyl, hydroxy, cyano, nitro, alkyl or alkoxy; a cyclic 3-6 membered ring alkylene or 5-6 membered ring alkenylene or benzyl optionally substituted with halogen, trihalomethyl, alkyl, hydroxy, alkoxy or cyano;   R 7  is an alkylene diradical having from 1 to 6 carbon atoms;   X and X' are each independently --O--, --S-- or --NR 2  --   L, M and N are each independently hydrogen, hydroxy, halogen, trihalomethyl, nitro, cyano, alkyl or alkoxy having from 1 to 4 carbon atoms and ##STR64## m has a value of from 1 to 6 and n in each instance has a value of from 0 to 1.   
     
     
       2. The herbicidal compound of claim 1 having the formula ##STR65## wherein X, X', R and R' are as defined in claim 1. 
     
     
       3. The herbicidal compound of claim 2 wherein X and X' are oxygen atoms and R is a lower alkylene diradical or --(CH 2  CH 2  O) p  --CH 2  CH 2  -- where p has a value of from 1 to 8. 
     
     
       4. The herbicidal compound of claim 2 wherein X and X' are --NR 2  -- and R 2  is hydrogen or lower alkyl. 
     
     
       5. The herbicidal compound of claim 1 which is 2-(methyloxalyloxy) ethyl 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoate. 
     
     
       6. The herbicidal compound of claim 1 which is 2-2-(methoxycarbonyl) propionyloxy ethyl 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoate. 
     
     
       7. The herbicidal compound of claim 1 which is 2-(ethyloxalyloxy) ethyl 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoate. 
     
     
       8. The herbicidal compound of claim 1 which is 2-(2,4-dichlorophenoxyacetoxy)ethyl 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoate. 
     
     
       9. The herbicidal compound of claim 1 which is 8-(2,4-dichlorophenoxyacetoxy)-3,6-dioxaoctyl 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoate. 
     
     
       10. The herbicidal compound of claim 1 having the formula ##STR66## wherein R is an aliphatic diradical having 1 to 6 carbon atoms selected from the group of alkylene diradical or an alkylene diradical interrupted by an oxygen atom and R 4  and R 5  are each independently lower alkyl, phenyl or halogenated phenyl. 
     
     
       11. The herbicidal compound of claim 10 which is 2-(N,N-dimethylsulfamoyloxy)ethyl 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoate. 
     
     
       12. A herbicidal composition comprising an effective amount of a compound of claim 1 and an inert carrier. 
     
     
       13. A process for controlling undesirable plant growth which comprises applying to the plant or plant situs a growth controlling amount of the herbicidal compound of claim 1. 
     
     
       14. The process of claim 13 wherein the herbicidal compound is applied at a rate of between about 0.05 and about 8 pounds per acre. 
     
     
       15. The process of claim 13 wherein the herbicidal compound is applied in combination with an inert carrier as a liquid spray. 
     
     
       16. The process of claim 13 wherein herbicidal compound is applied in combination with an inert solid carrier as a dust or granulated mixture. 
     
     
       17. The process of claim 13 wherein the compound of claim 1 is applied as a post emergent treatment. 
     
     
       18. The process of claim 13 wherein the compound of claim 1 is applied as a pre emergent treatment. 
     
     
       19. The herbicidal compound of claim 1 where X and X' are oxygen; n is 1; R is an ethylene radical and R 1  is ##STR67## 
     
     
       20. The herbicidal compound of claim 19 where R 3  is ##STR68## m is 2 and n is 0. 
     
     
       21. The herbicidal compound of claim 20 having the formula ##STR69##